Water → 3-Chloro-4-methanesulfonyl-benzaldehyde

HRID 1532288Notes

Reaction equation

HRID 1532288 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[Cl:10].[Na+].[CH3:12][S:13]([O-:15])=[O:14].O>CS(C)=O>[Cl:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[S:13]([CH3:12])(=[O:15])=[O:14])[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 227103,4-DichlorobenzaldehydeHCID 2733271Sodium methanesulfinate

Product 1

HCID 117361153-Chloro-4-methanesulfonyl-benzaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution containing 1.0 g of 4,3-dichlorobenzaldehyde in 45 ml of DMSO was added 1.93 g of methanesulfinicacid sodium salt with stirring at 90° C. The solution was stirred for 6 hours at 90° C. and then poured into water. Sodiumhydrogencarbonate was added and the product was extracted with ethyl acetate. The extract was evaporated to dryness in vacuo. The residue was triturated with 2-propanol, yield 1.06 g. 1H-NMR (DMSO-d6,400 MHz): 3.45 (s, 3 H, CH3), 8.09-8.27 (m, 3 H, Ar), 10.01 (d, 1 H, CHO).

Workup

  1. stirringThe solution was stirred for 6 hours at 90° C.
  2. additionSodiumhydrogencarbonate was added
  3. extractionthe product was extracted with ethyl acetate
  4. customThe extract was evaporated to dryness in vacuo
  5. customThe residue was triturated with 2-propanol, yield 1.06 g

Sources & evidence

ORD record
ord-3417f8a3bbd9432290244b8ad3c223ec
Source dataset
uspto-grants-2001_03
Patent number
US06201027B1

Reaction notes

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